2-(2-aminoethyl)-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium chloride | 864270-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(2-aminoethyl)-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium chloride
• 英文别名: methyl 2-(2-aminoethyl)-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium-5-carboxylate;chloride
• CAS: 864270-08-6
• 化学式: C₂₀H₂₀N₃O₂*Cl
• 分子量: 369.851
• InChiKey: APOQOYWTORVRHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-琥珀酰亚胺基 N-甲基氨基甲酸酯 、 2-(2-aminoethyl)-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium chloride 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以78%的产率得到methyl 11-methyl-2-[2-(methylcarbamoylamino)ethyl]-6H-pyrido[4,3-b]carbazol-2-ium-5-carboxylate;chloride
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032
• 作为产物：
  描述：

  2-(N-Boc-2-aminoethyl)-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium chloride 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 以97%的产率得到2-(2-aminoethyl)-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium chloride
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives

  摘要：

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.032

文献信息

• Determination of binding modes and binding constants for the complexes of 6H-pyrido[4,3-b]carbazole derivatives with DNA
  作者：Akihito Shimazu、Masashi Kawagoshi、Shoichi Takeda、Haruaki Kurasaki、Asako Kato、Nahoko Morii、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.bmc.2016.12.031

  日期：2017.2

  The binding modes and binding constants for the complexes of forty types of pyridocarbazole derivatives 1–40 with double stranded DNAs (dsDNAs) were reported. The binding modes were determined by a combination of a deflection spectroscopy and orientation of the corresponding molecule in the DNA-based film with chain alignment. All of the compounds exhibited the intercalation-binding mode. Its binding

  对于40种pyridocarbazole衍生物的复合物的结合模式和结合常数1 - 40报告，其中双链DNA的（dsDNAs）。通过偏转光谱和基于DNA的膜中相应分子的取向与链排列的组合来确定结合模式。所有化合物均表现出插层结合模式。根据吡啶并咔唑骨架上的取代基和dsDNA的序列，通过石英晶体微量天平（QCM）测定的其对于络合物的结合常数K a从1.7×10 5到4.5×10 7  M -1变化。结合常数K a具有2-（ω-氨基）烷基和5-（ω-氨基）烷基氨基甲酰基的吡啶并咔唑衍生物的“α-羟基”大于相应的ω-脲基衍生物的β-羟基。这些ω-氨基化合物在络合中表现出强烈的GC碱基对偏好。随着NaCl浓度的增加，K a值降低。通过分子模型阐明，2系ω-氨基衍生物的骨架与堆积的GC碱基对完全重叠，从而导致形成稳定的嵌入复合物，以及5系脲基的骨架衍生物半重叠导致形成不稳定的络合物。此外，ln K a
• Synthesis and in vitro antitumor activity of novel 2-alkyl-5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazol-2-ium and 2-alkylellipticin-2-ium chloride derivatives
  作者：Ryota Mori、Asako Kato、Kousuke Komenoi、Haruaki Kurasaki、Touru Iijima、Masashi Kawagoshi、Y.B. Kiran、Sho Takeda、Norio Sakai、Takeo Konakahara

  DOI：10.1016/j.ejmech.2014.05.032

  日期：2014.7

  Twenty-one types of novel ellipticine derivatives and pyridocarbazoles (5-methoxycarbonyl-11-methyl-6H-pyrido[4,3-b]carbazoles) with a nitrosourea moiety, linked by an oxydiethylene unit at the 2 position, were synthesized, and their cytotoxicity against HeLa S-3 cells was evaluated. Some of these new compounds exhibited potent antitumor activity by comparison with that of ellipticine. (C) 2014 Elsevier Masson SAS. All rights reserved.